邻炔基苯胺氢胺化合成轴手性吲哚研究进展

doi:10.6023/cjoc202401010

有机化学 ›› 2024, Vol. 44 ›› Issue (6): 1786-1792.DOI: 10.6023/cjoc202401010 上一篇下一篇

综述与进展

邻炔基苯胺氢胺化合成轴手性吲哚研究进展

王家晟^a,†, 王泽树^b,†, 何卫民^a^,^*(), 叶龙武^a^,^b^,^c^,^*()

a 南华大学化学化工学院湖南衡阳 421001
b 厦门大学化学化工学院福建厦门 361005
c 中国科学院上海有机化学研究所金属有机化学国家重点实验室上海 200032

收稿日期:2024-01-12 修回日期:2024-02-23 发布日期:2024-03-12
作者简介:
^†共同第一作者
基金资助:
国家自然科学基金(22125108); 湖南省科技创新计划(2023RC4004)

Research Progress on the Hydroamination of o-Alkynylanilines for the Synthesis of Axially Chiral Indoles

Jiasheng Wang^a,†, Zeshu Wang^b,†, Weimin He^a,*(), Longwu Ye^a^,^b^,^c,*()

a College of Chemistry and Chemical Engineering, Nanhua University, Hengyang, Hunan 421001
b College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, Fujian 361005
c State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032

Received:2024-01-12 Revised:2024-02-23 Published:2024-03-12
Contact: * E-mail: weiminhe@usc.edu.cn; longwuye@xmu.edu.cn
About author:
^†These authors contributed equally to this work.
Supported by:
National Natural Science Foundation of China(22125108); Science and Technology Innovation Program of Hunan Province(2023RC4004)

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摘要/Abstract

邻炔基苯胺的氢胺化反应是合成吲哚的一种重要方法. 在此基础上, 具有一定位阻取代基的邻炔基苯胺在手性过渡金属或者有机小分子催化下, 可以发生阻旋选择性5-endo-dig环化, 从而合成重要的轴手性吲哚化合物. 以不对称氢胺化反应产物中的手性轴分类, 系统介绍了含C—N、C—C以及N—N手性轴的吲哚化合物的催化不对称合成方法.

关键词: 不对称催化, 氢胺化反应, 轴手性吲哚, 炔烃

Hydroamination of o-alkynylanilines is an important approach for the synthesis of indoles. On this basis, o-alkynylanilines bearing substituents with certain steric hindrance could undergo chiral transition-metal catalyzed or organocatalytic atroposelective 5-endo-dig cyclolization for the synthesis of axially chiral indoles. Classified by the types of chiral axes in the products of enantioselective hydroamination, the catalytic enantioselective methods for the preparation of axially chiral indoles containing C—N, C—C and N—N chiral axes are systematically introduced.

Key words: asymmetric catalysis, hydroamination reaction, axially chiral indole, alkyne

引用此文

王家晟, 王泽树, 何卫民, 叶龙武. 邻炔基苯胺氢胺化合成轴手性吲哚研究进展[J]. 有机化学, 2024, 44(6): 1786-1792.

Jiasheng Wang, Zeshu Wang, Weimin He, Longwu Ye. Research Progress on the Hydroamination of o-Alkynylanilines for the Synthesis of Axially Chiral Indoles[J]. Chinese Journal of Organic Chemistry, 2024, 44(6): 1786-1792.

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图/表 10

图1. 天然产物中和手性催化剂及配体中的轴手性吲哚骨架

Figure 1. Axially chiral indole-based skeletons in natural products and chiral catalysts and ligands

图式1. 邻炔基苯胺氢胺化合成轴手性吲哚

Scheme 1. Hydroamination of o-alkynylanilines for the synthesis of axially chiral indoles

图式2. 钯催化邻炔基苯胺氢胺化合成C—N轴手性吲哚

Scheme 2. Palladium-catalyzed hydroamination of o-alkynyl- anilines for the synthesis of C—N axially chiral indoles

图式3. 手性Br?nsted酸催化炔酰胺氢胺化合成C—N轴手性吲哚

Scheme 3. Chiral Br?nsted acid-catalyzed hydroamination of ynamides for the synthesis of C—N axially chiral indoles

图式4. 有机催化邻炔基苯胺氢胺化合成C—C轴手性吲哚

Scheme 4. Organocatalytic hydroamination of o-alkynylanilines for the synthesis of C—C axially chiral indoles

图式5. 银催化邻炔基苯胺氢胺化合成C—C轴手性吲哚

Scheme 5. Silver-catalyzed hydroamination of o-alkynylanilines for the synthesis of C—C axially chiral indoles

图式6. 钯催化邻炔基苯胺氢胺化合成N—N轴手性吲哚

Scheme 6. Palladium-catalyzed hydroamination of o-alkynyl- anilines for the synthesis of N—N axially chiral indoles

图式7. 手性Br?nsted酸催化邻炔基苯胺氢胺化合成N—N轴手性吲哚

Scheme 7. Chiral Br?nsted acid-catalyzed hydroamination of o-alkynylanilines for synthesis of N—N axially chiral indoles

图式8. 邻炔基苯胺的不对称氢胺化合成C—N、C—C及 N—N轴手性吲哚

Scheme 8. Asymmetric hydroamination of o-alkynylanilines for the synthesis of C—N, C—C and N—N axially chiral indoles

图式9. 通过邻炔基苯胺氢胺化合成的轴手性吲哚在不对称催化中的应用

Scheme 9. Applications of axially chiral indoles synthesized from the hydroamination of o-alkynylanilines in asymmetric catalysis (Zhao, C.)

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邻炔基苯胺氢胺化合成轴手性吲哚研究进展

Research Progress on the Hydroamination of o-Alkynylanilines for the Synthesis of Axially Chiral Indoles

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